Family-friendly holiday rentals in Chappaquiddick Island

Perfect house for 8 guests (we had 10 guests one night, but they had to sleep on a pull out couch). The pool and hot tub in the backyard is awesome for a summer getaway. Tons of common space/living areas, wish we were able to use it more! Kitchen has everything you need. The layout is pretty unique and took a bit to get used to, but it added to the overall charm. I would definitely stay here again and recommend it for a long weekend (we were here for a wedding and made a weekend out of it) or if you’re looking for a getaway to the Cape for a week. Great location too!

Great place. Very central to Main Street. Quiet, plenty of space, good parking, easy communication and check-in. We will come again!

Great stay! Place is in a quiet residential area, yet centrally located and easy to get places. Nice yard and hot tub was a plus (clean and good temp). We didn’t have a chance to use the fire pit, but outdoor furniture and sitting area was nice with space for everyone. House was very clean, beds comfortable. Host was very responsive. Would definitely stay again.

Super responsive, great host. Very friendly, offered us the local newspaper with deals on places to go and everything. incredible space, right along the water. Thank you, Ron!

Nice private house with lots of bedrooms, a pool and nice grounds. House was very clean. We had a great time with our family. Can walk to a few places in town, but need to get into the car for most. The Dennis beaches were great and just a short drive away. Would recommend this place for families. The house has access to Scargo Lake, which is nice, but it is a bit of a hike down a good-sized hill. Host was nice and responsive to questions.

I had a wonderful experience staying at this Airbnb. The place was exactly as described—clean, cozy, and well-stocked with all the essentials. The host was friendly, responsive, and made check-in and out super easy. The neighborhood was quiet and felt very safe, with great local spots just a short walk or drive away. I’d absolutely stay here again and recommend it to anyone looking for a comfortable and convenient stay!

We stayed at this home with a group of five people and the home fit everyone great. The view from the home of the marsh is beautiful and we spent Saturday hanging out on the dock. It is really peaceful and we had an amazing time. Michele was a pleasure to work with and was very accommodating with being flexible for check in and check out times. Thank you again!

We visited Island Grace for a long weekend and enjoyed the many perks of this beautiful home! It was a perfect spot to visit Edgartown, Oak Bluffs, and beaches and just a short drive to other areas and towns. We enjoyed biking, the hot tub, and the well-appointed kitchen. The beds were so comfortable! We truly had everything we needed and thought it was so fun to watch their HGTV episode!

Location was great and the neighborhood was quiet and beautiful. Robert was very responsive and accommodating. The ease of finding the home & access with the great directions along with a bottle of wine in the fridge were added bonuses after driving all day/night and a late night arrival.

Adorable cottage, nice lay out, very clean with all of the comforts of home, a dishwasher, brand new stove, nice size fridge with ice maker. This cottage has a private backyard with grill and new teak patio set and lounge chairs for relaxing and soaking up the sun, the window boxes are a nice touch to add to the cottage charm! Beautiful location near 2 very nice beaches, peaceful neighborhood near the Cape Cod Canal for morning or afternoon walks and bike rides. Great restaurants close by, The Lobster Trap and Trading Post lounge are my favorites, also a great little store right down the street, Gray Gables Market has everything you would need for your stay. We loved our stay, can’t wait to visit again!

My husband and I absolutely adored Lia and Michael’s cottage! It was so perfect for a long weekend away. The place was extremely clean, and was well equipped with anything and everything we needed for our stay (and then some). The location was also great and was bikeable/walkable to the beach and some local cafes we went to daily. Really feel like we hit the jackpot with this find on a holiday weekend. Would absolutely love to stay again!

Stayed here for 1 night while working on the island. What a beautiful set up and it is in a great location to walk to town. The place was very clean and Brian is super helpful should you need anything! Will be looking to book again next time we are on island.

Very pleasant. Kristen oferred earlier checkin and very late checkout which allowed us to enjoy some additional hours at the beach and kayaking

Lisa's place is so lovely. It is so peaceful and has a great view. Check in was super easy and everything was as expected. Lisa is a great communicator and we were easily able to get questions answered. When we had an issue (not related to our stay) Lisa was so helpful and kind. Highly recommend.

Loretta’s house is very comfortable and at a quiet and convenient location.

Perfect location. Host was there to even be sure I got a spot right in front of the cottage because it was busy time around there. Very clean and in tip top shape. Will definitely book there again.

Lovely home and well outfitted for our stay. Conveniently located on well maintained grounds.

This was our family's first visit to the Cape, and the first time that mom had been back in decades. We had a wonderful stay! Mashpee was a great location - there was local access to good beaches and restaurants; but also a great location to access Sandwich and the Canal, Falmouth, Woods Hole and the Islands, all the way to Provincetown and everything in between. And we took advantage of it all over the week we stayed. Ed was a wonderful host! From booking until we checked out, he was very communicative, friendly, and had great information about local attractions and specialties. The property was very comfortable, and big enough for our family to relax and recharge. And our son loved the heated pool! We would definitely rent this or any of Ed's properties again!

We stayed in the tree house suite. It had a lovely deck surrounded by trees and a great view of the sky. Craig and Ginny are as friendly a couple you will ever meet--always quick to answer questions and offer some great suggestions, Craig even offered to drop us off at a few places. They were so kind they felt like old friends. The beach is beautiful and a five minute walk away--which is great because they charge 25 bucks to park. So do the easy walk, and Ginny will provide chairs, towels, and umbrellas. Hyannis itself is a great place to walk around with lots of shops and great restaurants. We also took a ferry to Nantucket which was delightful, as well. I would visit them again without question. Go. You won't be disappointed. Michael and Rebecca

Barbara’s condo was roomy and comfortable. We fell in love with the screened in porch. Lovely room for a cup of coffee in the mornings and a glass of wine in the late afternoon. We took a short ride through the woods to the town beach which led us to beautiful views of Tashmoo. We had a great time!

The home was pristine, more than what we could have asked for. Shelly was an amazing host, again, more than we could have asked for. You want a gorgeous home, with a stellar host, in the cape, with a private pool, amazing amenities, on a golf course and very close to the beaches, fun spots for kids, and shops, go to this place.

Lovely location and very clean. Good spot to travel qround island. Lambert Cove was beautiful at sunset. If you have a bad back you might want to bring a mattress pad.

The Condo was clean & comfortable. Having two bedrooms with queen beds was perfect for us, and sharing the 1 bathroom worked fine. The price was better than most other options. It was peaceful, and very quiet during our stay (in early May). Having the pool available would be very nice in summer months.

Beautiful house. Kid friendly Really close to the beach Amazing hosts